Three of his books, Rich Dad Poor Dad, Rich Dad's CASHFLOW Quadrant, and Rich Dad's Guide to Investing, have been on number one on the top 10 best-seller lists simultaneously on The Wall Street Journal, USA Today and the New York Times. Rich Kid Smart Kid was published in 2001, with the intent to help parents teach their children financial concepts. He has created three "Cashflow" board and software games for adults and children and has a series of "Rich Dad" CDs and disks.

In 1977, Kiyosaki entered the retailing industry. He started a company that brought to market the first nylon and Velcro "surfer" wallets. The company was moderately successful, but eventually went bankrupt, as he wanted to save money on costs and did not intellectually protect the product. In the early 1980s, Kiyosaki started a business that licensed T-shirts for heavy metalrock bands such as Mötley Crüe. The company went bankrupt in 1985.[8] In his book You can Choose to be Rich, Kiyosaki said that after his bankruptcy, he became homeless and was living with his then girlfriend Kim at the back of an old Toyota for several months before starting their own business from the ground up.[9]

Aside from operating the Rich Dad Company and Cashflow Technologies, Inc., Kiyosaki continues to operate external business ventures and various investments, since he came out of retirement in 1997. Many of these ventures are concentrated in the information technology (mobile apps and internet), publishing, retail, education, mining, energy, financial market, and real estate industries.[14][14]

Starting with small residential real estate investments back in 1973, Kiyosaki began investing in small condos on the island of Maui, making a small profit from capital gains by the mid-1970s. Kiyosaki starting his own real estate holding company in the 1980s during his tenure with Xerox and continued on with smaller real estate investments after the Savings and loan crisis and the 1986 Tax Reform Act hit the United States in the early 1990s, where much foreclosure investment real estate was sold for pennies on the dollar. After progressing with smaller real estate investments, Kiyosaki moved into the commercial real estate business, branching off into semi-large apartment complexes, with a large portion concentrated in Arizona and the Southwestern United States and retired in 1994.

Since coming out of retirement in 1997, Kiyosaki remains involved with the apartment business and stated in an interview with Jason Hartman in 2011, that he owns over 1400 units of apartment houses.[16][17] Kiyosaki has been involved with commercial real estate sector such as investing in warehouses, Triple net lease and real estate development ventures around the United States.[18][19]

Kiyosaki has stated in a Rich Dad video, several interviews, and on a number of Yahoo Finance articles that he owns oil drilling operations and oil wells around the United States, but does not invest in oil company shares such as ExxonMobil or BP.[20][21][21][22]

In his book Rich Dad Poor Dad, Kiyosaki mentioned achieving consistent 16% ROI through tax lien certificates.[23] Written in a chapter of Rich Dad's Prophecy, Kiyosaki states of having invested in various government tax free bonds such as municipal bonds and municipal mortgage real estate investment trusts offered by real estate development companies paying over 12% tax-free dividend interest.[24]

Kiyosaki has also stated in interviews that he does not invest or play the stock market, much like the fact that he does not invest in oil company stocks. Instead, Kiyosaki trades stock options, Forex currencies, and other derivatives in the financial markets as stated in a chapter written in his book, Rich Dad's Prophecy and in a 2009 interview with real estate investor John Hartman.[17] Kiyosaki has mentioned investing in hedge funds, private placements, and other various funds such as private equity funds typically investments reserved by SEC law only for millionaires or high-income individuals. Written in a chapter of Rich Dad's Prophecy, Kiyosaki also states that he invests in IPO's and developing small cap stocks. Some of the various companies he has invested in include a consumer products company, a silver company, an oil company that eventually went bankrupt, and a gold company.[25]

Kiyosaki is involved in the commodity market where he invests in gold and silver commodities as well as gold and silver ETF's, as written in chapter of his 2008 book, "Rich Dads, Increase Your Financial IQ". He stated this for the reason that he uses commodities as a hedge against uncertain economic forces such as inflation and hyperinflation as well as government's mismanagement via printing of the nation's currency.[23]

Kiyosaki's financial and business teachings focus on what he calls "financial education" generating passive income by means of business and investment opportunities, such as real estate investments, businesses, stocks and commodities, with the ultimate goal of being able to support oneself by such investments alone and thus achieving true financial independence without working for a paycheck through a traditional salaried job. Kiyosaki defines the term "assets" as things that generate cash inflow, such as stock dividends, rental income from properties, or income from businesses, and the term "liabilities" as things that devour cash, such as houses, cars, and so on. Kiyosaki argues that financial leverage is critically important in becoming rich, despite the inherent financial risks, instability, insecurity, repercussions, and pitfalls that come with it.

Originally self-published before being picked up commercially to become a best seller, the central concept of his book, "Rich Dad, Poor Dad" is an anecdotal comparison of his "two fathers." His "poor dad" was his biological father, who was highly educated and became superintendent of the Hawaii State Department of Education but was always struggling financially. Contrasted with this is his "rich dad," who was his best friend's father,a successful businessman who later became "one of the richest man in Hawaii" by investing the income from his businesses into income-producing investments such as real estate, and was a high school dropout. Its main purpose as a self-help book is to help people rethink their idea of money and their concept of themselves as employees who will gain financial rewards from conformity and education.

Kiyosaki uses the "rich dad, poor dad" comparison to illustrate his view that the majority of people are stuck in what he refers to as "the rat race"–living paycheck to paycheck and spending all of their time working to pay bills and other expenses. In his books, Kiyosaki advocates tax-advantaged investment vehicles, such as real estate or businesses, rather than ownership of securities such as stocks and mutual funds. This idea is further developed in his later books and "Rich Dad" became Kiyosaki's personal brand for various publishing ventures.

Kiyosaki's business approach stresses the importance of financial literacy through the acquisition of what he calls "assets" as the means to obtaining wealth. He says that life skills are often best learned through experience and that there are important lessons not taught in school. He says that formal education is primarily for those seeking to be employees or self-employed individuals, and that this is an "Industrial Age idea." In order to obtain financial freedom, one must be either a business owner, an investor, or both generating passive income, particularly on a monthly basis. Kiyosaki stresses the importance of entrepreneurship and focusing on looking for business opportunities instead of jobs, the importance of turning earned income into passive and portfolio income, and learning to read financial statements. With regards to business, Kiyosaki states that roughly 80% of the very rich became rich through building a business, stressing the study the basics of business and entrepreneurship such as learning how to sell, brand and market in order to be a rich investor and good business owner, or to know what a business owner knows.

Kiyosaki often refers to what he calls "The CASHFLOW Quadrant", a conceptual tool which he developed to categorize the four major ways income is earned in the world of money. Depicted in a diagram, this concept entails four groupings, split with two crossed lines (one vertical and one horizontal). In each of the four groups there is a letter representing a way in which an individual may earn income. The letters are as follows.

B: Business owner – A person who owns a business to make money; typically where the owner's physical presence is not required.

I: Investor – Investing money in order to receive a larger income in the future or analyzes other businesses as potential investments.

For those on the left side of the divide (E and S), Kiyosaki says that they may never obtain true wealth. Conversely, those on the right side of the divide (B and I) are supposedly following the only road to true wealth. Kiyosaki also classifies the four main "asset" classes as means of gaining wealth:[26]

Commodities: Gold, silver, iron ore, or copper that are used to hedge government's mismanagement printing of the nation's currency.

Kiyosaki wrote in one column that investors in any mutual fund with a 2.5% annual fee would, over a long time period, surrender 80% of the earnings to the fund.[27] Kiyosaki expanded on his criticism of mutual funds in another column by stating they are for "losers."[28] Despite the fact that most mutual funds actually charged less than 1.1%.[29] He has drawn much criticism for comparing investing in mutual funds to playing the lottery, and for discouraging 401(k) investing, contrary to the advice of most professional financial advisers.[30] In contrast to these statements, Kiyosaki wrote in his book Prophecy that while mutual funds are not great investments, they remain one of the few acceptable investment vehicles available to those who will not educate themselves financially.

Kiyosaki's criticisms are supported by the founder of the mutual fund Vanguard, John C. Bogle. In a Frontline episode titled "401(k)s: The New Retirement Plan, For Better or Worse", Bogle stated that management fees and trading costs gobble up approximately 2.5% of an investor's annual returns and approximately 80% of an investor's long term gains. He says management costs reduce the value of a $1,000 investment over 65 years from approximately $140,000 at 8% compounded annually to a mere $30,000 at 5.5% compounded annually. Bogle's solution is to utilize index funds, which charge as little as 0.09%, to substantially reduce or eliminate management fees.[31]

Kiyosaki advocates the value of games, particularly Monopoly, as tools for learning basic financial strategies such as "trade four green houses for one red hotel." Kiyosaki has created several games such as Cashflow 101 and Cashflow 202 to reinforce the information in his book.

Many local stations of the Public Broadcasting Service (PBS), including WTTW of Chicago, KAET of Phoenix, KOCE of Orange County, California, WLIW of the New York/New Jersey area, and WGBH of Boston, featured Kiyosaki with his now cancelled Rich Dad TV series. His latest TV special was a fund-raising drive. During this television special, Rich Dad's Guide to Wealth with Robert Kiyosaki, he provides viewers with financial education, opposing the common notion of getting a college degree and downplaying the importance of attaining academic or professional education to achieve financial success.

In 2006, Kiyosaki appeared on CNBC, discussing financial issues, answering questions from the audience, and comments by the financial experts were also invited. In particular, Kiyosaki also filled in a few episodes under the title The Millionaire Inside Debt-Free and The Millionaire Inside: Get Inspired. Other financial experts accompanied Kiyosaki, including David Bach, Jennifer Openshaw, Larry Winget, Keith Ferrazi, and Dr. Laura Morgan Roberts.[42][43]

In 2009, Kiyosaki was featured in a 10 Questions session in Time magazine.[44] Kiyosaki has criticized other financial gurus, particularly the financial teachings of Suze Orman and Jean Chatzky, calling it "bad advice". Orman responded to Kiyosaki's attacks via Twitter and the two engaged in a Twitter war in March 2010.[45]

In 2013, Kiyosaki began hosting his own online radio show, where it focuses on his personal views on money, entrepreneurship, business, personal development and the global economy. With his personal frustration with financial advice being dispelled by financial pundits in mainstream financial and business media, Kiyosaki began envisioning his own radio show with his own team of professionals from the world of money, investing, business, and personal development. The show also hosts his wife, Kim Kiyosaki, special guests, as well as Rich Dad advisers where they provide various viewpoints on setting the foundation for financial prosperity.[46]

Kiyosaki has 3 younger siblings: Emi Kiyosaki (b.1948), Jon Kiyosaki (b.1949), and Beth Kiyosaki (b.1951). Emi Kiyosaki, is a former Tibetan Buddhistnun who was then known by the name Ven. Tenzin Kacho. He has co-authored one book with Emy called "Rich Brother, Rich Sister".

Kiyosaki's mother, a nurse died suddenly of heart failure in March 1971. His father, a schoolteacher and a long-time smoker, died of lung cancer in 1991.

Kiyosaki's books and teachings have been criticized for focusing on anecdotes and containing little in the way of concrete advice on how readers should proceed.[47] Kiyosaki responds that his material is meant to be more of a motivational tool to get readers thinking about money rather than a step-by-step guide to wealth. He also says the books are supposed to be "interesting" to people, which precludes involving a lot of technical material.[48]

In 2010, the Canadian Broadcasting Corporation investigated the Rich Dad seminars associated with Kiyosaki on their consumer advocacy program, Marketplace.[49] They found that one-day free seminars were conducted at which three-day courses were offered for $500. At the three-day classes, participants were offered longer courses priced between $12,000 and $45,000. A hidden camera was employed at a $500 seminar in Kitchener, Ontario, showing the trainer, Marc Mousseau, advising participants to request that their credit-card limits be raised and giving out scripts with instructions on how to ask for limits as high as $100,000.[50]

The show interviewed Bob Aaron,[51] a lawyer whose practice is 90% real estate law, who said that some of Mousseau's advice was unusual and unlikely to work, such as advising that a developer might give two condos free when selling ten, getting an option to buy the house at a later date, and buying a house in pre-foreclosure.[50] The program also found a claim by the trainer to be untrue; he claimed to have been part of a deal that made $32 million on a mobile home park in Saskatchewan, but the park did not exist. The instructor was described as "overbearing, obnoxious, and rude" by an attendee, after showing video footage of his behavior.[49]

When questioned about the findings of the program, Kiyosaki said he too was unhappy about how the company running the seminars, Tigrent Learning (formerly Whitney International), was conducting them and that these were not the first complaints he had heard. He promised to look into the problems and said they would serve as "ammunition I need" in his "continuing to pressure them" and "constantly saying" to Tigrent Learning that he is "unhappy with them". He claims not to have known "how severe it was" at the time of partnering with them that Tigrent Learning had such a "checkered past". "I'm more upset than you are; I really am," he told the interviewer, "It disturbs me. It's not my fault."[50]

On August 20, 2012, one of Kiyosaki's companies, Rich Global LLC, filed for bankruptcy in Wyoming Bankruptcy Court.[52] The move followed a ruling by a U.S. District Court jury that former business partners of Kiyosaki were entitled to $23,687,957.21 of the profits from events they helped to set up for Kiyosaki including a 2002 appearance at New York's Madison Square Garden. A spokesman for Kiyosaki asserted that the amount of the award exceeded the value of Rich Global LLC and that Kiyosaki would not use money from outside the company to meet the judgement.[53]